Volume 20, Issue 22
Natural Products
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ChemInform Abstract: Stereoselectivity in the Formation of Unsaturated Wittig Products and Stereospecificity in Their Electrophile-Induced Cyclization to C-Glycosides.

F. J. LOPEZ HERRERA

F. J. LOPEZ HERRERA

Dep. Bioquim. Biol. Mol. Quim. Org., Univ. Malaga, 29071 Malaga, Spain

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M. S. PINO GONZALEZ

M. S. PINO GONZALEZ

Dep. Bioquim. Biol. Mol. Quim. Org., Univ. Malaga, 29071 Malaga, Spain

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M. NIETO SAMPEDRO

M. NIETO SAMPEDRO

Dep. Bioquim. Biol. Mol. Quim. Org., Univ. Malaga, 29071 Malaga, Spain

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R. M. DOMINGUEZ ACIEGO

R. M. DOMINGUEZ ACIEGO

Dep. Bioquim. Biol. Mol. Quim. Org., Univ. Malaga, 29071 Malaga, Spain

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First published: May 30, 1989

Abstract

The reaction of the ribofuranose (I) with the phosphorane (II) leads to Z/E mixtures (IIIa) + (IIIb) depending on the reaction conditions, whereas only the E isomer (VII) is obtained from the mannofuranose (VI).

ChemInform Abstract

The reaction of the ribofuranose (I) with the phosphorane (II) leads to Z/E mixtures (IIIa) + (IIIb) depending on the reaction conditions, whereas only the E isomer (VII) is obtained from the mannofuranose (VI). Cyclization reactions of (IIIa), (IIIb), and (VII) with iodine provide the iodo compounds (IV), (V) and (VIII). In addition, the iodide (IV) can be transformed to the dianhydroheptonate (IX).

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